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Literature summary for 3.1.1.8 extracted from

  • Wieckowska, A.; Wieckowski, K.; Bajda, M.; Brus, B.; Salat, K.; Czerwinska, P.; Gobec, S.; Filipek, B.; Malawska, B.
    Synthesis of new N-benzylpiperidine derivatives as cholinesterase inhibitors with beta-amyloid anti-aggregation properties and beneficial effects on memory in vivo (2015), Bioorg. Med. Chem., 23, 2445-2457 .
    View publication on PubMed
Search for more literature for 3.1.1.8

Application

Application Comment Organism
drug development acetylcholinesterase, butyrylcholinesterase and beta-amyloid are the predominant biological targets in the search for anti-Alzheimer's agents Equus caballus

Inhibitors

Inhibitors Comment Organism Structure
1-(2-fluorobenzyl)-N-[6-(1H-indol-1-yl)hexyl]piperidin-4-amine
-
 Equus caballus
1-(2-fluorobenzyl)-N-[8-(1H-indol-1-yl)octyl]piperidin-4-amine
-
 Equus caballus
1-(3-chlorobenzyl)-N-[6-(1H-indol-1-yl)hexyl]piperidin-4-amine
-
 Equus caballus
1-(3-chlorobenzyl)-N-[8-(1H-indol-1-yl)octyl]piperidin-4-amine
-
 Equus caballus
1-benzyl-N-[3-(2,3-dihydro-1H-indol-1-yl)propyl]piperidin-4-amine
-
 Equus caballus
1-benzyl-N-[5-(2,3-dihydro-1H-indol-1-yl)pentyl]piperidin-4-amine
-
 Equus caballus
1-benzyl-N-[6-(1H-indol-1-yl)hexyl]piperidin-4-amine
-
 Equus caballus
1-benzyl-N-[8-(1H-indol-1-yl)octyl]piperidin-4-amine
-
 Equus caballus
2-(3-[[1-(2-fluorobenzyl)piperidin-4-yl]amino]propyl)-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
2-(3-[[1-(3-chlorobenzyl)piperidin-4-yl]amino]propyl)-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
2-(3-[[1-(4-hydroxybenzyl)piperidin-4-yl]amino]propyl)-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
2-(3-[[1-(4-methoxybenzyl)piperidin-4-yl]amino]propyl)-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
2-(6-[[1-(2-fluorobenzyl)piperidin-4-yl]amino]hexyl)-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
2-(6-[[1-(3-chlorobenzyl)piperidin-4-yl]amino]hexyl)-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
2-(6-[[1-(4-hydroxybenzyl)piperidin-4-yl]amino]hexyl)-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
2-(6-[[1-(4-methoxybenzyl)piperidin-4-yl]amino]hexyl)-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
2-(8-[[1-(2-fluorobenzyl)piperidin-4-yl]amino]octyl)-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
2-(8-[[1-(3-chlorobenzyl)piperidin-4-yl]amino]octyl)-1H-isoindole-1,3(2H)-dione a selective BChE inhibitor Equus caballus
2-(8-[[1-(4-hydroxybenzyl)piperidin-4-yl]amino]octyl)-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
2-(8-[[1-(4-methoxybenzyl)piperidin-4-yl]amino]octyl)-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
2-[3-[(1-benzylpiperidin-4-yl)amino]propyl]-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
2-[5-[(1-benzylpiperidin-4-yl)amino]pentyl]-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
2-[6-[(1-benzylpiperidin-4-yl)amino]hexyl]-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
2-[8-[(1-benzylpiperidin-4-yl)amino]octyl]-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
4-[(4-[[6-(1H-indol-1-yl)hexyl]amino]piperidin-1-yl)methyl]phenol
-
 Equus caballus
4-[(4-[[8-(1H-indol-1-yl)octyl]amino]piperidin-1-yl)methyl]phenol
-
 Equus caballus
donepezil
-
 Equus caballus
additional information evaluation of a combination of both anticholinesterase and beta-amyloid anti-aggregation activities in one molecule, and therapeutic potential in vivo. Design and synthesis of 28 compounds as derivatives of donepezil that contain the N-benzylpiperidine moiety combined with the phthalimide or indole moieties. No or poor inhibition by 2-[5-[(1-benzylpiperidin-4-yl)amino]pentyl]-1H-isoindole-1,3(2H)-dione Equus caballus
N-[6-(1H-indol-1-yl)hexyl]-1-(4-methoxybenzyl)piperidin-4-amine
-
 Equus caballus
N-[8-(1H-indol-1-yl)octyl]-1-(4-methoxybenzyl)piperidin-4-amine
-
 Equus caballus
tacrine
-
 Equus caballus

Organism

Organism UniProt Comment Textmining
Equus caballus P81908
-
-

Source Tissue

Source Tissue Comment Organism Textmining
commercial preparation
-
 Equus caballus
-
serum
-
 Equus caballus
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
butyrylthiocholine + H2O
-
 Equus caballus thiocholine + butyrate
-
 ?

Synonyms

Synonyms Comment Organism
butyrylcholinesterase
-
 Equus caballus

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
25
-
 assay at Equus caballus

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
8
-
 assay at Equus caballus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00034
-
 pH 8.0, 25°C Equus caballus 4-[(4-[[8-(1H-indol-1-yl)octyl]amino]piperidin-1-yl)methyl]phenol
0.00052
-
 pH 8.0, 25°C Equus caballus 4-[(4-[[6-(1H-indol-1-yl)hexyl]amino]piperidin-1-yl)methyl]phenol
0.00072
-
 pH 8.0, 25°C Equus caballus 2-(8-[[1-(3-chlorobenzyl)piperidin-4-yl]amino]octyl)-1H-isoindole-1,3(2H)-dione
0.00075
-
 pH 8.0, 25°C Equus caballus 1-(2-fluorobenzyl)-N-[8-(1H-indol-1-yl)octyl]piperidin-4-amine
0.00081
-
 pH 8.0, 25°C Equus caballus 2-(8-[[1-(4-hydroxybenzyl)piperidin-4-yl]amino]octyl)-1H-isoindole-1,3(2H)-dione
0.00083
-
 pH 8.0, 25°C Equus caballus 1-(2-fluorobenzyl)-N-[6-(1H-indol-1-yl)hexyl]piperidin-4-amine
0.00093
-
 pH 8.0, 25°C Equus caballus 1-benzyl-N-[8-(1H-indol-1-yl)octyl]piperidin-4-amine
0.00108
-
 pH 8.0, 25°C Equus caballus 1-benzyl-N-[5-(2,3-dihydro-1H-indol-1-yl)pentyl]piperidin-4-amine
0.00133
-
 pH 8.0, 25°C Equus caballus 1-(3-chlorobenzyl)-N-[8-(1H-indol-1-yl)octyl]piperidin-4-amine
0.00178
-
 pH 8.0, 25°C Equus caballus 1-(3-chlorobenzyl)-N-[6-(1H-indol-1-yl)hexyl]piperidin-4-amine
0.00187
-
 pH 8.0, 25°C Equus caballus 2-(8-[[1-(2-fluorobenzyl)piperidin-4-yl]amino]octyl)-1H-isoindole-1,3(2H)-dione
0.00198
-
 pH 8.0, 25°C Equus caballus 2-[8-[(1-benzylpiperidin-4-yl)amino]octyl]-1H-isoindole-1,3(2H)-dione
0.00232
-
 pH 8.0, 25°C Equus caballus 2-(6-[[1-(4-hydroxybenzyl)piperidin-4-yl]amino]hexyl)-1H-isoindole-1,3(2H)-dione
0.00273
-
 pH 8.0, 25°C Equus caballus 2-(6-[[1-(3-chlorobenzyl)piperidin-4-yl]amino]hexyl)-1H-isoindole-1,3(2H)-dione
0.00341
-
 pH 8.0, 25°C Equus caballus 1-benzyl-N-[6-(1H-indol-1-yl)hexyl]piperidin-4-amine
0.004
-
 pH 8.0, 25°C Equus caballus 2-(6-[[1-(2-fluorobenzyl)piperidin-4-yl]amino]hexyl)-1H-isoindole-1,3(2H)-dione
0.00446
-
 pH 8.0, 25°C Equus caballus N-[8-(1H-indol-1-yl)octyl]-1-(4-methoxybenzyl)piperidin-4-amine
0.00453
-
 pH 8.0, 25°C Equus caballus 2-(3-[[1-(3-chlorobenzyl)piperidin-4-yl]amino]propyl)-1H-isoindole-1,3(2H)-dione
0.00565
-
 pH 8.0, 25°C Equus caballus 2-(8-[[1-(4-methoxybenzyl)piperidin-4-yl]amino]octyl)-1H-isoindole-1,3(2H)-dione
0.00739
-
 pH 8.0, 25°C Equus caballus 2-(6-[[1-(4-methoxybenzyl)piperidin-4-yl]amino]hexyl)-1H-isoindole-1,3(2H)-dione
0.00813
-
 pH 8.0, 25°C Equus caballus N-[6-(1H-indol-1-yl)hexyl]-1-(4-methoxybenzyl)piperidin-4-amine
0.00937
-
 pH 8.0, 25°C Equus caballus 2-(3-[[1-(4-hydroxybenzyl)piperidin-4-yl]amino]propyl)-1H-isoindole-1,3(2H)-dione
0.01052
-
 pH 8.0, 25°C Equus caballus 2-(3-[[1-(2-fluorobenzyl)piperidin-4-yl]amino]propyl)-1H-isoindole-1,3(2H)-dione
0.01285
-
 pH 8.0, 25°C Equus caballus 2-[6-[(1-benzylpiperidin-4-yl)amino]hexyl]-1H-isoindole-1,3(2H)-dione
0.0153
-
 pH 8.0, 25°C Equus caballus 1-benzyl-N-[3-(2,3-dihydro-1H-indol-1-yl)propyl]piperidin-4-amine
0.0268
-
 pH 8.0, 25°C Equus caballus 2-(3-[[1-(4-methoxybenzyl)piperidin-4-yl]amino]propyl)-1H-isoindole-1,3(2H)-dione
0.0518
-
 pH 8.0, 25°C Equus caballus 2-[3-[(1-benzylpiperidin-4-yl)amino]propyl]-1H-isoindole-1,3(2H)-dione